3,4-Thiophenediacetonitrile, 2,5-dimethyl- → [2,5-Dimethyl-4-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-thiophen-3-yl]-acetonitrile

HRID 900982

Reaction equation

HRID 900982 reaction equation
[C:1]([CH2:3][C:4]1[C:5]([CH2:11][C:12]#[N:13])=[C:6]([CH3:10])[S:7][C:8]=1[CH3:9])#[N:2].Cl.N[C:16]1[C:21]([F:22])=[C:20]([F:23])[CH:19]=[C:18]([F:24])[C:17]=1[SH:25]>CCO>[CH3:9][C:8]1[S:7][C:6]([CH3:10])=[C:5]([CH2:11][C:12]2[S:25][C:17]3[C:18]([F:24])=[CH:19][C:20]([F:23])=[C:21]([F:22])[C:16]=3[N:13]=2)[C:4]=1[CH2:3][C:1]#[N:2]

Participants

4

Reactant 2

HCID 8190183,4-Thiophenediacetonitrile, 2,5-dimethyl-HCID 11390282Benzenethiol, 2-amino-3,4,6-trifluoro-, hydrochloride

Product 1

HCID 59698813[2,5-Dimethyl-4-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-thiophen-3-yl]-acetonitrileYield 31.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (4-cyanomethyl-2,5-dimethyl-thiophen-3-yl)-acetonitrile (1.90 g, 10.0 mmol) and 2-amino-3,4,6-trifluoro-benzenethiol hydrochloride (2.16 g, 10.0 mmol) in EtOH (22 mL) is heated to reflux for 44 h. After cooling to room temperature, the mixture is concentrated in vacuo and purified by flash chromatography (silica gel, 10-30% ethyl acetate in heptane). Further purification by recrystallization with ethyl acetate and heptane gave [2,5-dimethyl-4-(4,5,7-trifluoro-benzothiazol-2-ylmethyl)-thiophen-3-yl]-acetonitrile (1.1 g, 31.2%) as a white powder: mp 145-146° C.; Rf 0.54 (30% ethyl acetate in heptane); 1H NMR (CDCl3, 300 MHz) δ 6.95-7.08 (m, 1 H), 4.36 (s, 2 H), 3.59 (s, 2 H), 2.43 (s, 3 H), 2.41 (s, 3 H).

Workup

  1. temperatureto reflux for 44 h
  2. concentrationthe mixture is concentrated in vacuo
  3. custompurified by flash chromatography (silica gel, 10-30% ethyl acetate in heptane)
  4. customFurther purification
  5. customby recrystallization with ethyl acetate and heptane

Sources & evidence

ORD record
ord-c767adab3d1a47d98d79fc17ebadb3bd
Source dataset
uspto-grants-2008_04
Patent number
US07361671B2

Linked notes

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